


Regrets and Second Chances

by cordelia_kingsbridge



Series: Boston Verse [12]
Category: Original Work
Genre: Aftercare, Age Difference, BDSM, College, Come Shot, Dirty Talk, Dom/sub, Humiliation, Interracial Relationship, M/M, Minor Feminization, Promiscuity, Rough Sex, Safewords, Sex Toys, Size Difference, Size Kink, Slut Shaming, Subspace
Language: English
Status: Completed
Published: 2016-12-12
Updated: 2016-12-12
Packaged: 2018-09-08 04:23:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 9,263
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8830336
Author URL: https://archiveofourown.org/users/cordelia_kingsbridge/pseuds/cordelia_kingsbridge
Summary: After Riley's sexy encounter with his ex-boyfriend, he and Andres have a conversation that's been a long time coming.





	

**Author's Note:**

> It’s been a long wait since the last installment, but on the upside, this is the longest fic in the Boston ‘verse to date!
> 
>  **Additional content warnings** : This story includes underage drinking (by U.S. standards), sex while mildly intoxicated, and graphic descriptions of consensual sex two characters engaged in while under the age of eighteen.

“Um…” Riley drummed his fingers against his glass. “Never have I ever had sex with a woman.”

This was met with a chorus of good-natured boos and raspberries. Riley grinned as every guy in the circle besides himself and Dylan took a drink, as did a few of the girls.

“That’s cheating,” Hector said, pointing an accusing and slightly wobbly finger in Riley’s direction.

“ _How?_ ” Riley said.

“All right, all right,” said Chase, who was sitting to Riley’s left. “My turn. I’ll get him back, don’t worry.” He paused for dramatic effect, then said, “Never have I ever been fucked in the ass.”

Everyone whooped. Riley rolled his eyes, lifted his rum and Coke to his lips, and took a small sip – then tilted his head back for several long, exaggerated gulps that brought forth peals of delighted laughter around the circle.

“That’s a damn dirty lie, by the way,” Sabrina said to Chase. She flipped her long braids behind one shoulder.

Chase’s jaw dropped. “What? No, it’s not – ”

“I know what you got up to this summer with that hottie from Bethesda Prep – ”

While Sabrina and Chase argued over whether he had, in fact, let the hottie from their rival school peg his ass, Riley watched who else in the game was drinking. Some of the girls, which wasn’t surprising – and Dylan, blushing bright red and ducking his head like he hoped nobody would notice.

Riley blinked. When he and Dylan had started dating, Dylan had been a virgin in every sense of the word; he’d never so much as had someone touch his cock before. Riley, on the other hand, had already happily hooked up with dozens of guys even by then.

He had been Dylan’s first for everything, from handjobs and blowjobs to showing Dylan how to properly finger him and, after a few months, to fuck him. He’d fingered Dylan sometimes while sucking him off, and he would rim him every once in a while when Dylan asked for it. But Riley had never fucked him.

Though Dylan had been curious about switching, Riley had never had the desire to top in his entire life. He’d known that he wouldn’t be able to stay hard for it, and he hadn’t wanted to embarrass either himself or Dylan by trying. Dylan had never pushed him for more, of course.

It seemed he’d been getting up to some interesting activities at Dartmouth, though. Riley took an unsteady breath, his cock stirring in his jeans. He didn’t want to top Dylan himself, but the thought of him getting fucked by some college guy was undeniably hot.

The game only got dirtier from there, and Riley was pleasantly tipsy by the time they wrapped things up and everyone wandered their separate ways. He mixed himself another drink and ended up chatting on a sofa with Sabrina and Hector.

Elyse’s house had been the site of many a wild high school party. Her parents were constantly traveling for work, and seemed to think nothing of leaving their teenage daughter unsupervised in an enormous mansion full of booze and empty bedrooms. Now, the Saturday night after Thanksgiving, practically everyone in Riley’s graduating class had gathered for one more blowout before returning to their respective colleges.

Hector was pulled away after a few minutes by some old swim teammates, and Dylan approached soon afterward, gesturing to the empty space. “Okay if I sit?”

“Of course,” Riley said. He ran appreciative eyes over Dylan, who looked mouthwatering in black jeans and a form-fitting sweater.

Dylan settled beside him, smiling, and Riley smiled back. Sabrina cleared her throat.

“I should probably check on Melissa,” she said. “She looked a little queasy earlier. See ya!”

With that, Sabrina took off. Riley rolled his eyes and said, “Subtle.”

“You have to admit it’s a little weird.” Dylan set his drink aside on the end table – on top of a coaster, naturally. “All of us hanging out together again after you and I broke up?”

“We only broke up because we knew the long-distance thing wouldn’t work for us. There’s no reason we can’t still be friends.”

“Before the other day, you and I hadn’t spoken in three months,” Dylan said, a hint of reproach in his tone. “I miss you.”

“I miss you too.” Riley sighed. “That’s _why_ we haven’t spoken. The way I handle losing you is to try not to think about you at all. If we still talked, it would be too difficult. Maybe someday things will be different.”

Dylan’s face glowed as if lit from within. Riley put his own drink on the coffee table, then tucked his legs up underneath himself and turned toward him, inching a little closer. The magnetic pull he’d always felt to Dylan was as powerful as ever, and his buzz wasn’t doing anything for his impulse control.

“So you finally got a chance to bottom?” he asked.

Dylan blushed adorably and dropped his eyes to the couch. “Yeah. It was a guy I met at a party a couple of months ago.” He glanced up at Riley and quickly added, “Nothing serious. Just a hookup.”

“Did you like it?” Riley wondered what the guy had looked like – big buff jock or more on the twinky side? What position had they fucked in? Dylan would look good taking it from behind –

“Yeah, it was fun,” Dylan said. “Not more fun than topping, but I’d want to do it again. I guess I like both.”

“Cool,” said Riley. He was glad Dylan’s first experience being fucked had been a positive one. His own first time had been incredible, but he’d heard horror stories from other guys that made him wince just thinking about them.

“Have you, uh… have you been with anyone?” Dylan asked, trying and failing to sound nonchalant.

“A few.” There was no way Riley was telling his ex-boyfriend that in the three months they’d been broken up, he’d already slept with so many guys that he’d literally lost count.

“They’re lucky.” Dylan wore all his emotions on his face, open and honest, and Riley couldn’t resist him anymore.

Sliding closer so his knees brushed Dylan’s leg, Riley put a hand on Dylan’s thigh and leaned in. “How many times do you think we’ve had sex in this house?”

Dylan made a strangled noise. “I don’t know. Twenty, thirty? Maybe more.”

“Do you remember when you fucked me over the hood of Elyse’s dad’s Porsche in the garage?”

“God, how could I forget that? Haley and that guy she was dating walked in on us, and you just told me to keep going.”

“Of course I did.” Riley nuzzled his throat. “It felt so good.”

Dylan’s pulse was racing. Riley dragged his hand up Dylan’s inner thigh to fondle his cock, finding him half-hard.

“Riley,” Dylan said, breathless.

“Do you want me to stop?” Riley asked, groping him through his jeans right there on the couch in front of everyone.

“No.” Dylan looped one arm around Riley’s shoulders, cupped his jaw with his other hand, and pulled him into a kiss.

It was sweet and familiar, reminding Riley of a thousand kisses just like it. He rubbed up against Dylan’s side, massaging his cock as the kiss deepened, until he grew frustrated with the angle and swung himself onto Dylan’s lap.

Dylan’s hands went right for Riley’s ass. When they’d been dating, he’d never been able to stay away from it for long; he’d constantly been grabbing it, squeezing it, sliding his hand into Riley’s back pocket when they were in public. Riley had _adored_ that about him.

“Fuck,” Dylan mumbled into Riley’s mouth while he kneaded the firm muscles. “Your ass got even rounder. How is that physically possible?”

Riley grinned. He pulled back a bit and started rolling his hips, undulating against Dylan in a way that frotted their cocks together even as it pushed his ass back against Dylan’s hands.

“You gave it to me so hard that night in the garage,” he said.

Groaning, Dylan said, “I remember. You were screaming – the echo – ”

They both shuddered and dove back into the kiss, more urgently this time.

“You owe me ten bucks,” Hector said somewhere to Riley’s left. “I told you they couldn’t make it through this weekend without hooking up.”

Riley ignored him; he didn’t care who saw him and Dylan making out, and he knew Dylan didn’t either. Their frequent and enthusiastic PDA had been a fond running joke their entire last two years of high school.

Having Dylan’s tongue in his mouth and Dylan's hands all over his ass was driving Riley to distraction, though. He was quickly approaching the point of no return, so he broke the kiss and said, “Are you gonna fuck me?”

“You want me to?” Dylan asked. His eyes were glazed with lust.

“Yeah.” Riley wasn’t wasted enough to think it was a good idea to sleep with the ex-boyfriend he still had feelings for, but he _was_ wasted enough not to care.

They scrambled off the couch, still kissing and groping each other, and stumbled out of the rec room towards the grand foyer. Somehow they made it up the Cinderella staircase without breaking their necks and headed for the guest bedrooms in the east wing.

A few of the doors were closed, and a couple more stood open despite the people unabashedly fucking inside. Riley and Dylan continued on until they found an empty bedroom, shutting the door by way of Dylan shoving Riley up against it.

After they stripped each other out of their shirts, Riley steered Dylan towards the bed, fumbling his belt and fly open. They banged into the foot of the mattress just as Riley was pushing his hand down the front of Dylan’s jeans.

Dylan grunted, his hips bucking. “Shit, could you wear your jeans any tighter?” he said, struggling with the task of getting his own hands into Riley’s pants.

Riley laughed, and they disentangled themselves long enough to get rid of the rest of their clothes. Naked, they tumbled together onto the bed, where Riley rolled Dylan onto his back and rutted against him.

Dylan’s busy hands roamed over Riley’s ass, down his thighs to pull his legs farther apart, and then back up, fingers running along the crack. Riley moaned his appreciation when Dylan’s fingertips grazed his hole.

“Do you still carry lube in your wallet?” said Dylan.

“Mmm-hmm.” Riley buried his face in the crook of Dylan’s shoulder, enjoying the sensation of Dylan rubbing and stroking all around his rim.

A few seconds passed like that, and then Dylan said, “Are you going to get it?” in an amused voice.

“Ugh,” Riley said. He wanted to get fucked more than he didn’t want to move, though, so he got up and retrieved his wallet from his fallen jeans. As usual, he had a condom and a couple packets of lube tucked into the billfold, and he brought them back to the bed.

This time, he lay on his back, while Dylan stretched out on his side so they could kiss while Dylan fingered him. Riley pulled his knees up to his chest to give him unrestricted access.

“Was that your favorite time?” Dylan asked, two fingers deep in Riley’s ass.

“What?”

“When we had sex in Elyse’s garage. Was that your favorite time?”

“Oh. No. Top five, definitely, but not my favorite.” Riley sighed happily as Dylan’s fingers nudged his prostate. “The summer between junior and senior year, there was that week when you and I were fighting – ”

“Yeah. I don’t remember what about, though.”

“Me neither,” said Riley, which was a lie. “Toby McMillan was having a pool party. You and I were yelling at each other, really angry, and I stormed off. You followed me into the outdoor shower and fucked me against the wall.”

That was the roughest and most aggressive Dylan had ever been with him. Just thinking about it suffused Riley with a warm, submissive glow.

“Mmm, yeah, that was a good one.” Dylan’s fingers sped up, plunging in and out of Riley’s ass.

“What was your favorite?”

“Senior prom,” Dylan said without hesitation. “You sucked my cock in the limo and let me come on your face.”

Riley rubbed his thumb over Dylan’s lower lip. “I like it when you come on me.”

“And then when we got out, your mouth was all red and swollen, and everyone knew exactly what you’d been doing – ” Dylan broke off there, biting the ball of Riley’s shoulder to stifle a moan.

That was what had really excited him about the encounter, Riley knew. He’d always had an exhibitionist streak, which Riley had been more than happy to indulge.

Worked up to a fever pitch by the memories, Riley pushed Dylan’s hand away and said, “Get in me.”

Dylan put on the condom, and once they’d stuffed a pillow under Riley’s hips, he entered him easily in one long, smooth slide. They were about the same height, which made for a comfortable missionary position; Riley could get his legs up as high as he needed for the best angle, and it was effortless for them to kiss while they rocked together.

Sex with Dylan had always been different – special. There was an emotional dimension to it that Riley had never experienced with his other hookups during high school. He didn’t believe that people had to be in love for sex to be great, but there was no denying that love gave sex a particular beauty. He felt that beauty with Dylan, that tender, transcendent closeness, and he treasured it.

But there had always been something missing.

Though Dylan couldn’t be described as submissive, he didn’t have a drop of Dominant blood in his body. Riley had known that from the beginning, and he’d never tried to force or even coax Dylan to be something he wasn’t, no matter how much it frustrated him.

It hadn’t always been a problem. Riley didn’t need or want to be dominated every time he had sex – plus, Dylan was gorgeous and genuinely great in bed. Yet despite all the qualities that made sex with Dylan wonderful, despite how much Riley enjoyed it, he couldn’t honestly say he’d been satisfied.

He wasn’t satisfied now.

Riley held Dylan’s face with both hands and met his eyes. “I thought you missed me?”

“I do,” Dylan said. His pupils were blown wide, his cheeks flushed.

“Then _show_ me.” Dropping his hands to Dylan’s hips, Riley urged him into a faster pace. “Fuck me as hard as you can, babe, come on. I want to feel it tomorrow. I want to be sitting on that plane back to Boston still thinking about how you owned my ass in this bed.”

Dylan let out a shocked groan and surged forward, thrusting hard and rough into Riley’s ass. Riley gasped in pleasure.

“Yeah, God, just like that,” he said. “Give me everything you’ve got, come on, come _on_ – ”

They were both panting harshly, their sweating bodies straining against each other as Dylan pounded Riley into the mattress and Riley arched up into it. They kissed sloppily, hands grasping and clutching wherever they could reach.

“I’m close,” Dylan warned him.

Riley was closer. He grabbed his own cock and tugged it ruthlessly until his orgasm crashed through him a few seconds later, making him writhe and cry out. Dylan didn’t let up at all, prolonging the ecstasy as Riley’s body shuddered with immediate aftershocks.

When he came back to himself, he saw that Dylan was right on the edge, face screwed up in anticipation of release. He pressed a hand to Dylan’s chest and said, “Wait, wait, stop.”

Dylan’s hips juddered to a halt and he made a noise of pure agony.

“Pull out,” Riley said. “Pull out and come on my stomach.”

His jaw falling slack, Dylan thrust deep into Riley’s ass one more time before withdrawing and stripping off the condom. He braced himself over Riley on one hand and jerked himself off with the other at a furious pace.

Riley watched the flushed, leaking tip poking out through Dylan’s fist, his mouth watering. He wished they didn’t have to worry about safe sex; then he could have Dylan come on his hole and his mouth, taste it, feel it inside –

Dylan shouted when he came, long strings of come shooting over Riley’s abdomen to join the mess left there by his own release. Riley’s back bowed off the bed to meet it. After the first few spurts, Dylan’s hand slowed, coaxing out a couple last slow pulses to splash on Riley’s navel. Even once he was done, he kept soothing his cock with one hand, staring at Riley’s come-splattered body.

Riley dragged his fingers through their commingled semen. “Fuck,” he said with feeling.

His breathing labored, Dylan rolled off to the side and collapsed on his back. They lay in silence for a while basking in the afterglow, Riley idly tracing patterns on his drenched stomach.

“I still love you,” Dylan said.

Riley closed his eyes and swallowed hard. “I love you too.”

The mattress shifted as Dylan scooted closer, resting a hand on Riley’s chest. “So why did we break up? We can make it work.”

“We can’t,” Riley said, opening his eyes. “You know that; we talked about this for weeks. Keep dating while we go to college in different states? That never works for anybody. We said we wouldn’t be that stupid.”

“We – ”

Riley kissed him. “We’re drunk, and our brains are soaked in oxytocin right now. Things will feel different tomorrow.”

“You’re right,” said Dylan. He sighed and leaned his forehead against Riley’s. “It just… it hurts.”

“I know. I feel it too.” Riley smoothed his clean hand over Dylan’s jaw and down the side of his neck. “I fantasize about it, us staying together despite the distance. But we’re both too busy to visit each other on weekends, so we’d only ever be with each other over the holidays. I couldn’t go that long without seeing you, without touching you. And honestly, I don’t think I could go that long without sex.”

“We were apart for weeks last summer while you did that session at Cornell and I was in Belize. And then again this summer when you were on your adventure trek in Alaska and I was at Oxford. You went without sex for a long time then.”

Riley tensed involuntarily; to hide his reaction, he kissed Dylan once more and then sat upright. “That was different. Those were temporary separations with predefined end dates. This separation would be essentially permanent – even after college, there’s no guarantee we’d end up in the same place. I have no idea where I’ll go to medical school, or do my residency – ”

“I know,” Dylan said, squeezing Riley’s knee. “I’m sorry. I don’t mean to be pushy.”

“It’s okay, I understand.” Riley gestured to his messy stomach. “I’m gonna clean up, and then we can talk about this some more if you want, all right?”

Dylan nodded. Riley left the bed and shut himself in the ensuite bathroom, where he grabbed a fancy guest towel and a bar of soap to scrub with.

He really did need to clean up, but what he needed more was time and space to get his head on straight. _I don’t think I could go that long without sex_ – what a stupid fucking thing to say, and not something that would have slipped out if he hadn’t been so drunk and well-fucked. For two years, he’d been so careful, so painstakingly vigilant to avoid any topic or statement or behavior that would call into question whether or not he’d been faithful.

Because of course he hadn’t been, and it would only destroy Dylan to find that out now.

* * *

_Sorry this is taking so long_ , Riley texted Andres from the baggage claim at Logan International. _Looks like my bag is literally going to be the last one off._

 _Don’t worry about it. I’m waiting at Arrivals. If security tries to kick me out, I have a badge I can show them._ Andres followed that up with the policeman emoji.

Chuckling, Riley returned his phone to his coat pocket and adjusted the strap of his laptop bag on his shoulder. He had to wait a few more minutes for his small suitcase to come around on the carousel; he grabbed it the second he saw it and headed outside into the biting wintry air.

The sky was overcast, threatening snow. Riley shivered as he scanned the curb, looking for Andres’ blue Honda. When he walked over, Andres got out to meet him.

Andres was bundled up in a handsome black wool overcoat that emphasized his height and the breadth of his shoulders. A knit scarf the color of a rich Merlot was tucked around his neck, and he wore black leather gloves and boots. The soft, warm smile on his face crinkled his eyes at the corners. He looked… beautiful.

Riley realized he hadn’t breathed for several seconds and took a startled gulp of cold air.

“Hey, gorgeous,” Andres said.

“Hi.” Riley dropped his suitcase on the sidewalk and caught hold of Andres’ scarf, tugging him down for a kiss. Andres wrapped one arm around his waist and lifted him right off his feet so their faces were level and they could kiss more easily.

They kept it PG-13, but even still, Riley was lightheaded by the time Andres set him down. He didn’t bother looking around to gauge the reactions of the other people on the curb. Screw them if they didn’t like it.

While Andres tossed Riley’s bags in the trunk, Riley got in the passenger’s seat, rubbing his hands together. Though it was still warm in the car, the first thing he said once Andres joined him was, “Can you turn my seat heater on?”

“You’re so sensitive to cold.” Andres turned the key in the ignition, cranked up the heat, and hit the button for the seat heater. “It’s because you’re such a tiny little thing.”

“Oh, fuck you,” Riley said, laughing. “Only one of us is an unusual size here, and I hate to break it to you, but it’s not me.”

Andres took hold of Riley’s wrist, wrapping his fingers all the way around it and then some. That in itself would have been enough to turn Riley on under ordinary circumstances; with Andres wearing leather gloves, it was like a kick to the gut. He stared at Andres’ hand encircling his wrist, his mouth dry, and wondered if he could talk Andres into fingering him with those gloves on.

“See?” Andres said smugly. “Tiny.”

“Look how far back you have to put your seat to fit your legs in this car, you giant,” Riley retorted.

Grinning, Andres let go of Riley’s wrist to lace their fingers together instead. “You hungry?”

“Yeah.” Riley squeezed his hand.

They went to a café near Andres’ apartment in the South End for a late lunch, trading stories of their Thanksgiving holidays. Andres was the youngest of five siblings, most of whom were married with kids, and he had an army of aunts, uncles, and cousins of various generations all living in the same neighborhood. The rowdy, chaotic scene he fondly described was worlds away from Riley’s own tranquil experience of nine people sitting around his parents’ massive dining room table.

He couldn’t take his eyes off Andres as they ate, drinking in every gesture and expression as if it’d been months rather than days since they’d last seen each other. Andres always moved with grace, aware of his own size and considerate of the effect it had on other people. He was friendly and respectful to their server, listened to Riley with genuine interest, and when the check came, he didn’t protest splitting it down the middle.

Riley wanted to climb into his lap and never leave.

In fact, he was so overwhelmed by what he was feeling that he fell quiet and preoccupied when they left the café. They went to Andres’ apartment, where Riley had already planned to stay the night, and spent about an hour hanging out with Jack and his girlfriend Sofia before they retired to Andres’ bedroom.

Once they were alone, Andres said, “Are you okay? It seems like something’s bothering you.”

“I’m fine. But there is something I need to talk to you about.”

“Sure.” Andres sat at the foot of his bed, dressed now in just a soft sweater and dark jeans, and looked at him expectantly.

Riley remained standing. “I slept with my ex-boyfriend last night.”

Andres’ only visible reaction was a sort of mild surprise. “That must’ve been weird.”

“Yeah. I mean, it was nice, but then he started talking about getting back together.” He saw the assumption forming on Andres’ face and added, “Which we didn’t! We were both a little drunk and sentimental, but we talked about this for weeks over the summer. We both know that breaking up was the right thing to do.”

“Okay,” Andres said. He tilted his head to the side. “This is your high school boyfriend, right? You never talk about him.”

“There’s a reason for that. And that’s what I want to talk to you about.” Riley realized he was wringing his hands and made himself stop. “There are things I haven’t told you about myself, because I – I like the way you look at me, and I didn’t want that to change.”

“You don’t have to tell me anything you don’t want.”

“I know. But you _deserve_ the truth at this point. I don’t want to be the kind of person who keeps secrets for selfish reasons.”

Andres nodded for him to continue, his expression solemn.

Riley cleared his throat. “Dylan started at my school our junior year, and we started dating pretty soon after we met. He was my first boyfriend. I was… head over heels for him. And for the first couple of months, everything was amazing. Perfect.”

“But?”

“But there were things I needed that he couldn’t give me,” Riley said quietly.

Comprehension dawned in Andres’ eyes. “He wasn’t Dominant.”

“Not at all. Early on, I sounded him out about it, and I knew it just wasn’t in his nature. I never tried harder than that, because I didn’t want to make him uncomfortable, or worse, scare him away.” Riley sighed. “Maybe I should have risked it anyway, I don’t know.”

“You cheated on him,” Andres said.

“Yeah. A friend’s older brother, Matt – he’s the guy who took my own virginity, the one who introduced me to BDSM – I scened with him while he was home from college. I felt so disgusting afterwards, not because of the sex, but because I’d betrayed Dylan. I swore I’d never do it again.”

Riley looked down at his hands and took a deep breath.

“I did it again,” he said. “And again and again and again, and every time it got a little easier, until eventually I stopped trying to talk myself out of it at all.” He met Andres’ eyes. “I’ve been with over a hundred guys, and most of that happened while I was in a relationship with a man who thought we were monogamous.”

Andres was quiet for a minute. “Dylan still doesn’t know?” he asked.

“He has no idea. I’ve thought about telling him, but it would ruin two years’ worth of memories for no good reason. It just seems cruel.” Riley crossed his arms over his chest and said, “I’ve done other things that I regret, but cheating on Dylan is the only thing I’ve ever done that I’m truly ashamed of.”

He waited anxiously for Andres’ judgment. What if he was so disgusted that he couldn’t bring himself to touch Riley again? What if he didn’t want to see him anymore?

“You know,” Andres said, “I tend to believe that the mistakes people make are less important than how they react to them. You were a teenager in your first relationship and you acted selfishly. I don’t care about that so much as I do about this: would you ever do it again?”

“God, no,” said Riley. “Never. I’d never even put myself in another position where that was a _possibility_.”

Andres shrugged. “So you made some bad mistakes, and then you learned and grew from them. That’s just part of being human. It doesn’t make me look at you any differently.”

A lump formed in Riley’s throat, and he couldn’t speak for a minute. “Sometimes I think you can’t be real,” he finally said.

With a startled laugh, Andres said, “Thanks. But I’ve got plenty of my own flaws – you’ve seen them.”

He held out his hands. Riley moved forward to take them, standing between his knees.

“Why’d you decide to tell me this now?” Andres asked.

Now that the burden of apprehension had been lifted from Riley’s shoulders, he could verbalize the thoughts he’d had when they left the café. “When we first met, this was just part of my past, something you had no reason or right to know. But over time, as we’ve gotten closer, it’s started feeling more like something I was actively hiding from you. I don’t want things to be like that between us.”

Andres lifted one of Riley’s hands to his mouth and kissed his knuckles. “You understand that there’s nothing wrong with not being able to get what you need from one person, right? It was breaking a promise to someone who trusted you that was wrong – not wanting or needing to have sex with other men.”

“That’s what I meant when I said I wouldn’t put myself in that position again. I know I didn’t just fuck those other guys because I needed to be dominated. I love sex, I love sleeping around, and I’d never be happy or satisfied being monogamous. It’s not in my nature any more than it was in Dylan’s to be Dominant. I won’t lie to anyone about that again.”

When Andres tugged on Riley’s hands, Riley slid onto his lap, straddling his thighs and looping his arms around Andres’ neck.

“Sorry if this is weird for you,” he said.

“Why would it be weird?” said Andres.

“Well, just because there’s no commitment between you and me doesn’t necessarily mean you want to hear about all the other guys I fuck on a regular basis.”

“Oh.” Andres glanced aside, a hint of red in his cheeks. “Um… Okay, since this is apparently an afternoon for confessions, there’s something I haven’t been totally forthcoming about.”

Riley hadn’t seen him flustered like this since the time he’d had Dom drop. “What?”

“Thinking about you with other guys turns me on.”

“You mean like that shower fantasy I told you about?”

“No. Well, yeah, obviously that too, but that’s not what I meant.” Andres blew out a breath and said, “I find your actual real-life promiscuity arousing. Thinking about you fucking your way across campus, having sex with any hot guy you want – it turns me on like crazy. I’m getting hard just talking about it right now.”

Riley could feel that. “You _like_ the fact that I sleep around a lot?” he said slowly. He could understand not having a problem with it either way, but to actively be aroused by it?

Andres shifted Riley into a more comfortable position on his lap, stroking his hipbones. “Yes. I’m not sure how well I can explain it, but… You’re so beautiful and self-confident, and you’re so uninhibited during sex – joyful, even. I like the thought of you going after what you want, getting filled with cock whenever you’re craving it, having your needs met so you’re always satisfied. That’s the sexiest thing in the world to me.” He lifted one shoulder self-consciously. “I know that’s weird – ”

“No,” Riley said, resting his fingers on Andres’ lips. “A little unusual, maybe, but not weird. I like it.”

“You do?”

“Mmm-hmm.” Riley pressed his own swelling erection against Andres’ stomach. He enjoyed indulging his own sluttiness, and knowing Andres got off on that too filled him with a hot excitement he’d never felt before. Tightening his arms around Andres’ neck, he said, “It makes me want you inside.”

Andres’ eyes darkened with lust, and his voice dipped lower into his Dom register. “If you haven’t had that pussy stuffed since last night, it’s probably aching by now.”

“Actually…” Riley squirmed on his lap. “There was this guy who was cruising me in the first-class lounge at the airport this morning – he fucked me in the bathroom before I got on the plane.”

“You _whore_ ,” Andres breathed, so reverently that it sounded like the most glowing of compliments. He seized Riley’s mouth in a forceful kiss.

They shed their clothing there at the foot of the bed, kissing all the while, Riley exulting in the rough, brutish way Andres manhandled him. When they were twined together stark naked, he pulled his mouth away from Andres’ long enough to say, “What about you?”

“What about me?” Andres smacked Riley’s ass, then grabbed a handful of the stinging flesh and kneaded until Riley whimpered.

“I want to hear about one of the guys you’ve hooked up with.”

Andres paused, his groping hand falling still. “Really?”

“Yeah.” Riley was eager to explore this new kink – sharing not only their fantasies, but real stories of their actual sexual exploits. He wanted to see if it would turn him on as much as it did Andres. “Please.”

“Okay. Come up here.”

The command was unnecessary, as Andres simply carried Riley with him to the other side of the bed. He sat against the headboard and arranged Riley on his lap again, facing the other way this time, so his chest pressed up against Riley’s back. Then he leaned over and grabbed a bottle of lube from the nightstand drawer.

“Should I tell you about the guy I picked up Friday night?” he asked.

Riley nodded, wriggling a bit to feel Andres’ huge, hard cock rubbing over his back.

“You’ve ruined me for twinks, you know.”

“Sorry,” Riley said unrepentantly.

“Sure you are.” Andres planted a hand between Riley’s shoulderblades and shoved him forward, so that Riley had to catch himself on the bed to keep from smashing into it. He held Riley there, bent at the waist, while he drizzled lube all over the small of Riley’s back and between his asscheeks. Then he yanked Riley back upright and made a satisfied noise as he frotted his cock through the newly slick skin.

Thrilled by the way Andres bullied him and threw him around, Riley pulled up his knees, placing his feet flat on the bed on either side of Andres’ thighs. The position left him exposed and vulnerable to Andres’ wandering hands.

“Anyway,” Andres said, “I’ve been going more for jock types lately. Luckily, all the colleges in this city means there’s never any shortage of hot athletic guys looking to get fucked.”

He teased Riley by stroking his cock with just three lubed fingers, which didn’t provide nearly enough pressure or friction.

“I met this one at Ignition on Friday night. White guy, baseball player, buff but not super-built. You know the type.”

Riley did, and he pictured it now – a handsome man a little taller than himself, muscular and broad through the shoulders, though still small in relation to Andres. His hair cut short and his skin tanned from long practices outside, winter be damned…

“I bought him a drink, and we got to talking.” Andres poured more lube directly onto Riley’s balls and massaged them. “Turns out he’d never been fucked before.”

Riley sucked in a breath. Was this… Had Andres taken a guy’s virginity on Friday night? Was that what this story was going to be about? His heart raced at the thought, heat flaring up his spine.

“He _wanted_ to – was fucking gagging for it, actually – but he’d never been able to bring himself to do it. All that pent-up, internalized homophobia and misogyny about it making him less of a man or some kind of bullshit.” As Andres spoke, he caressed Riley’s perineum and hole with the mix of casual dominance and tender affection that drove Riley insane.

“ _You_ don’t bottom,” Riley said, daring the impertinence because he wanted Andres to smack him down for it. He tilted his hips, straining to guide Andres’ fingers where he wanted them.

“Because I don’t like the way it feels, not because I have any mental hang-ups about it,” Andres said. “You know that. Don’t be a brat.”

He punctuated that command by pushing one finger three knuckles deep into Riley’s ass. Riley moaned and dropped his head back on Andres’ shoulder.

“He was all set to finally give it a try, so I brought him back here. We were messing around in the bed, working each other up, and everything was going great until – ”

“He got a good look at your monster cock and freaked out,” Riley said, panting through the sensation of Andres tapping his prostate.

“How’d you know?”

Riley snorted. “Let’s call it an educated guess.”

Slipping a second finger inside Riley, Andres alternated a gentle scissoring motion with deep, brisk pumping. He was still languidly rutting against the curve of Riley’s ass, his erection blazing hot.

“Well, ‘freaked out’ is a good way to describe it. It took me a few minutes to talk him down, remind him that we weren’t going to do anything he didn’t want and there was no rule that said we had to fuck. Once he’d calmed down a little, I laid him out on the bed and started giving him a blowjob.”

Andres found Riley’s prostate again and manipulated it more intensely. Riley whimpered, his hips jerking.

“ _That_ , he was totally into. Pretty soon, he’d relaxed enough for me to ask if I could rim him, which he’d never done before either.”

“You’re so good at that,” said Riley, meaning both rimjobs and the way Andres was working his prostate over like it was his job.

“Thanks.” Andres kissed Riley’s temple and added a third finger, giving Riley more of the intense stretch he craved. “So I ate out that tight little virgin ass, and he just melted. Wasn’t long before he was begging me to put my fingers in him.”

“Did you?”

“Of course I did. I always give my bottoms what they need.”

Proving his point, Andres rapidly corkscrewed his fingers in and out of Riley’s ass. He was becoming more aggressive by the moment, his breath warm against Riley’s ear, and Riley could feel sticky drops of precome joining the lube smeared across his ass and back.

His mouth roaming over Riley’s neck, Andres said, “I fingered him and licked him out while I jerked his cock, and he came that way, all over his own stomach.”

Riley groaned in sympathy with the fantasy. Andres suddenly pulled his fingers out, grasping Riley’s hips with both hands and urging him to get up on his knees. Then he steered one of Riley’s hands back to his ass, making his intent clear – he wanted Riley to kneel there and finger himself.

Deliciously embarrassed, Riley obeyed, sinking three fingers into his hole. It was challenging to keep himself upright on his knees without using his free hand to balance himself on the bed, so he spread his legs wider for a more stable base.

“I thought maybe he’d want to stop there,” Andres said, continuing his story. The slamming of the nightstand drawer was followed by the sound of tearing foil. “But having his ass played with had changed his mind again, and he wanted to get fucked. I put him on his hands and knees and fingered him until he was hard again, twitching his hips like a little slut, desperate to get something bigger inside.”

Andres moved Riley’s hand away. Taking hold of Riley’s hips again, he guided Riley backward onto his cock, sinking slowly but surely down the shaft. Riley moaned throatily the whole way.

“I knelt behind him, pushed in the head of my cock…” Andres seated Riley on his lap, so that Riley now knelt astride his thighs, his ass cradled by Andres’ hips, impaled to the hilt. “And that was as far as I got before his entire body tightened up. Clamped down on me like a vise.”

“He couldn’t take it like I do,” Riley said. He was deep in subspace and proud of the way his body had opened up for Andres with little resistance.

Andres squeezed his hips. “ _Nobody_ can take it like you do, baby. Greediest little pussy I’ve ever fucked.”

He began lazily rocking Riley back and forth on his cock, giving him no control over the pace or depth whatsoever. Riley relaxed into it and let himself be maneuvered as Andres willed.

“I worked him open nice and slow, fed him just an inch at a time,” Andres said. “He was moaning and gasping and squirming all over the place, going crazy for having his cherry popped. Took me a good ten minutes to get all the way inside.”

Firming his grip on Riley’s hips, Andres lifted him all the way up the length of his cock and dropped him back down. Then he did it again, and again, while Riley shivered and squealed in helpless pleasure.

“And then, as soon as I was balls-deep, he shot off again, just like that. Barely had a hand on his own dick.”

“Oh God,” Riley said.

“I started to pull out, but he begged me to keep going – wanted to get fucked for real.” Andres settled Riley on his lap again and directed his hips in a sinuous figure-eight movement, pressing his cock up against every sensitive spot inside Riley’s ass. “So I fucked him. Not as hard as I’d breed _your_ cunt, of course, but hard enough for him to feel like he was getting a good pounding. Had him with his face in the mattress and his ass in the air.”

Riley’s hole clenched at the imagery; he couldn’t help it. Hissing in response, Andres bent his own legs, shifting Riley’s weight backwards from his knees to his feet. Riley squatted over Andres’ lap, his legs forced wide by Andres’ muscular thighs, and braced himself on Andres’ knees while Andres bounced him on his cock.

“He was crying,” Andres said, breathing hard. “Not because he was afraid, or in pain, but because he was so overwhelmed. He was finally letting himself have something he’d denied himself for so long, and it wasn’t anything like what he’d expected. He hadn’t thought it would feel that good.” His voice cracked and went hoarse. “He kept – he kept thanking me while I fucked him – ”

They both groaned in unison.

“When I came, I shoved all the way inside…” Andres gave Riley a practical demonstration, bringing his ass down hard as he buried himself to the root. “And I stayed there while I jerked him off until he came a third time, all over the sheets.”

Flushed and dizzy, Riley said, “You took good care of him.”

“I hope so.”

Riley writhed on Andres’ lap, driven out of his mind by the story and the feeling of the huge cock so deep inside him. He wished hysterically that Andres had taken his own virginity, that his first experience on a man’s cock had been with this gorgeous, thick fucking beast that made him see stars. He’d probably have ended up an even bigger size queen than he was now.

“This position isn’t enough for you, is it?” Andres whispered into his ear. “You need me to ruin that cunt.”

“Yes, _please_ – ”

Andres lifted Riley off his cock. Riley whined at the loss, but when Andres ordered him on his hands and knees at the foot of the bed, he scrambled to comply. He arranged himself as whorishly as possible, with his legs spread obscenely wide and his back arched to push his ass up and out. Watching over his shoulder as Andres approached him from behind, he considered how intimidating the proud jut of that enormous erection must have been to Andres’ shy virgin baseball player.

Andres smacked Riley’s ass a couple of times, gripped both cheeks and jiggled them, and slapped the other side to even things out. Then he spread Riley’s ass apart and stared at his hole, licking his lips in a gesture that seemed unconscious.

“Please, you said you’d ruin it.” Riley flexed his hips provocatively.

“That’s right.” Slotting his cock between Riley’s asscheeks, Andres leaned over his back and smoothed his hands up Riley’s stomach to his chest, tweaking his nipples. “Is that what you need, baby? Need me to drill that pussy so hard you’re still sore tomorrow?”

“Yeah. Want everyone who looks at me to wonder why I’m limping.”

“Please. Nobody would have to wonder. Anyone who got a good look at your pretty cockslut body would know you spend all your free time getting stuffed with as many big dicks as you can get your hands on.”

With that, Andres straightened up and drove his cock into Riley’s ass once more. Riley shrieked, tossing his head back as his spine bowed into an even more exaggerated arch.

Standing at the edge of the bed gave Andres complete freedom of movement, and he put it to good use plowing Riley’s ass, hammering away like a sailor on shore leave. “Never have to hold back with you,” he growled. “Always take my cock like a perfect little fuckdoll, don’t you?”

Riley sobbed his wholehearted agreement.

Andres grabbed his shoulders for greater leverage – but a few moments later, his hips abruptly slowed. He ran his hands down Riley’s arms, then tugged on his elbows, pulling them back until Riley’s hands left the bed. Riley gasped when he realized what Andres wanted to do.

“Color?” Andres asked.

“Green.”

Andres hauled Riley further back and adjusted his grip. The end result was that Riley’s upper body hung suspended from Andres’ hands, entirely dependent on Andres to hold him up. If Andres let go, he’d faceplant right in the bed, with no time to catch himself.

Andres started thrusting – carefully at first, then ramping up in speed and force. Riley allowed his body to go slack, trusting to Andres’ strength, to his certainty that Andres would never, ever drop him.

He’d never been fucked like this before. It was one of the most degrading, objectifying positions he’d ever been in, because the way he just dangled in Andres’ grip, not supporting his own weight, meant he was totally helpless. He was being held in place, subjected to the brutal snaps of Andres’ hips, powerless to do anything but take it like the fuckdoll Andres had called him.

Moaning, he looked down at his own body. He felt a spine-tingling rush of humiliation at the sight of his neglected cock and balls bouncing around, his shaft smacking his stomach in time with Andres’ merciless thrusts. Since those few glancing touches earlier, Andres hadn’t laid a hand on Riley’s cock, far more interested in playing with his ass and getting inside him. And Riley… he _loved_ that, found it almost unbearably exciting when Andres ignored his cock in favor of his hole.

The pleasure welled up inside him, hot and electric, but the tipping point still caught him by surprise. He couldn’t ask permission or even warn Andres before his orgasm coiled up deep in his core and then exploded outward, streaking through every nerve ending, making him shake and cry out. His untouched erection jerked against his abdomen, shooting hard pulses of come into the empty air while his hole spasmed around Andres’ cock and clutched it tight.

“Oh, fuck,” Andres said in a low groan. “Fuck, yeah, that’s my little whore.”

He gently lowered Riley’s body flat on the bed, which meant Riley’s chest ended up smeared with his own come. Then he pinned Riley’s wrists to the mattress and slammed into him, his hips smacking ruthlessly off Riley’s ass.

Riley lay boneless beneath the assault, quaking with aftershocks that felt like mini-orgasms reverberating from his prostate. He felt so good that his ears were ringing and his vision was blurred.

As his thrusts lost their smooth rhythm, Andres said, “Tighten up that pussy. Milk my dick like a good boy, Riley, come on – ”

Riley did what he could with his weak muscles – which wasn’t much – but Andres was so far gone that it did the trick anyway. He ground his cock in circles inside Riley’s ass as he came, grunting and cursing, his hands like steel around Riley’s wrists. Once he’d spent himself, he thrust slowly in and out a few more times, then withdrew.

Before Riley could slide off the foot of the bed, Andres hitched him further up, until the mattress supported him from his shoulders to his upper thighs. “Stay like that,” Andres said as he moved away. “Keep your legs spread.”

Disobedience was the furthest thing from Riley’s mind. He remained exactly where and how Andres had placed him, zoning out altogether and startling back to awareness when Andres tapped his thigh.

“On your back. Hold your ankles.”

Riley rolled over and grabbed his ankles as instructed. He was flexible enough to hold them with his legs straight, but he thought Andres would like it more if he kept his knees bent and drawn toward his shoulders. It would look sluttier and put his body on better display – his skin sticky with come, lube dripping from his raw, plundered hole.

Andres moaned his approval, ghosting his fingers over Riley’s inner thighs. Then he showed Riley what he held in his other hand.

“No,” Riley said, his hole fluttering with need. “No, please, you can’t put that in me. It’s too big.”

The plug was a simple, classic spade shape, but much longer and thicker than was the norm. This was no cute toy that Riley could slip in and walk around with for hours – this one would make its presence known every single second it was inside him.

“It’s adorable that you think you have any control over what I do to you.” Andres eased the plug into Riley’s ass. He didn’t even need to spare a hand to spread Riley open, because Riley was already gaping for it.

“Don’t!” Panting, Riley stared down at where his body was hungrily swallowing the plug. “Please, sir, don’t… _no_ …”

He trailed off on a groan as Andres settled the base of the plug snug against his rim. He’d been fucked three times in the past twenty-four hours, and now his sore hole was forced wide around this thick plug, his body stuffed full. It felt so _good_ ; it was exactly what he needed. He gazed up at Andres and let out a helpless whimper.

Andres cupped Riley’s jaw and swept a thumb over his cheekbone. “I love this cock-drunk look you get on your face,” he said, his voice pitched low. “Cheeks all pink, eyes glazed over, mouth hanging open… It’s beautiful.”

He leaned down between Riley’s spread legs to kiss him. Riley was too euphoric to coordinate his own lips and tongue, so he just let Andres have his mouth, making soft purring noises in the back of his throat.

Pulling back, Andres said, “You can put your legs down now and relax, sweetheart.”

Riley lowered his legs, turned over, and made his slow, clumsy way up the bed, hampered by both the weight of the plug inside him and his dazed mental state.

 _Cock-drunk_ , Andres had called him. It was an apt description.

He collapsed face-first into the pillows and closed his eyes.

“Kind of early for bed, don’t you think?” Andres said, sounding amused.

“I need to rest for a while,” Riley mumbled. He was still in subspace, and he doubted he’d be surfacing any time soon. That was fine – he and Andres had done prolonged scenes before – but he had to take at least a short nap.

Andres helped shift Riley’s body around to get him under the covers and then joined him, though he sat up against the headboard rather than lie down himself. Riley snuggled closer, stretching himself along the length of Andres’ leg with one knee thrown over him and his head pillowed on Andres’ thigh. He sleepily caressed Andres’ soft, heavy cock, not with any intent to arouse, but just because it was right there in front of him.

One of Andres’ large hands roamed over his ass, occasionally nudging the plug; the other trailed across his face. “I’m sorry,” Riley said. “I came without permission. I didn’t mean to.”

“You never need my permission to come untouched. I don’t want you feeling like you have to control your sluttiness or keep it in check. You only have to ask permission when you need a hand on your cock to get you over the edge, all right?”

Andres pressed his fingers against Riley’s lips. Riley opened his mouth to suck on them, sighing in pure contentment.

“So you liked my story, then?” Andres asked.

“Mmm.”

“I’d like to hear your stories too, you know. If you wanted to tell me when you hook up with other guys, describe it to me – ”

That sounded good to Riley, but… He pulled off Andres’ fingers. “Could you – could you make it an order?”

There was a long pause before Andres said, “Really? You sure?”

Riley nodded. He knew his request crossed into unexplored territory between them. He was asking Andres to give him a permanent standing order, one that would affect his behavior even when they weren’t together. It implied a deeper, more intense connection than anything else they’d done so far. It was, in fact, something Riley had never done with any other man.

“All right.” Andres shoved his fingers back into Riley’s mouth, catching him off-guard, and squeezed his ass. His tone hardened, all Dom once more. “From now on, every time you let a man use one of your holes, you’re going to text me about it as soon as possible afterwards. You’ll tell me exactly what he did to you and how much you enjoyed it, so I can get off on hearing about what a needy little whore you are. Do you understand?”

Riley nodded again, his mouth crammed full of Andres’ fingers. He hunched his hips, pressing his groin up against Andres’ leg.

“If you’re a good boy, I might return the favor every now and then.”

Riley tried to speak and was thwarted by his mouthful. Andres withdrew his fingers.

“What was that?” he said.

“I want to be your favorite,” said Riley, nuzzling his thigh. “I don’t care how many guys you fuck, but I want to be your favorite one.” It was something he probably wouldn’t have said if he hadn’t been so blissed-out and submissive, but it was _true_ , so true it echoed all the way down to his bones.

He couldn’t see Andres’ face, but he felt the sudden tenderness in the way Andres’ fingers carded through his hair. “You are,” Andres said quietly.

Good. Riley curled tighter around Andres’ leg, thrumming with warmth and happiness. “You’re my favorite too,” he said, moments from falling asleep, and barely registered the long breath Andres exhaled in response.

**Author's Note:**

> Enjoying the Boston ‘verse? Check me out on [tumblr](http://ckingsbridge.tumblr.com) for updates, writing discussion, and information on my other works! You can also catch me on [Twitter](http://twitter.com/c_kingsbridge) and [Facebook](http://www.facebook.com/Cordelia.Kingsbridge).


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